Izmir Institute of Technology, Faculty of Science, Department of Chemistry, Urla-Izmir 35430, Turkey.
Bioorg Chem. 2010 Aug;38(4):139-43. doi: 10.1016/j.bioorg.2010.04.001. Epub 2010 Apr 9.
Synthesis of stilbene-fused chalcones and flavanones were successfully completed. Molecules were designed in a way to mimic the structural features of both "stilbene and chalcones" or "stilbene and flavanones" at the same time, and synthesized by three steps. Heck reactions of 3-bromobenzaldehyde with styrene derivatives gave corresponding (E)-stilbenes, which were reacted with acetophenones to furnish stilbene-fused 2'-hydroxychalcones under basic conditions. Finally, intramolecular cyclization reactions were performed to produce stilbene-fused flavanones.
二苯乙烯-查耳酮和二苯乙烯-黄酮的合成都取得了成功。这些分子的设计方式是同时模拟“二苯乙烯和查耳酮”或“二苯乙烯和黄酮”的结构特征,通过三步合成得到。3-溴苯甲醛与苯乙烯衍生物的 Heck 反应得到相应的(E)-二苯乙烯,在碱性条件下与苯乙酮反应得到二苯乙烯-并 2'-羟基查耳酮。最后,进行分子内环化反应得到二苯乙烯-并黄酮。